Imidazole → 5-Amino-2-(4-tert-butyldimethylsilyloxypiperidino)benzonitrile

HRID 1744529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744529
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12][CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[C:17]([Si:21](Cl)([CH2:24]C)[CH2:22]C)([CH3:20])([CH3:19])[CH3:18].N1C=CN=C1.C(=O)([O-])O.[Na+]>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:11][CH2:12][CH:13]([O:16][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:22])[CH2:14][CH2:15]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 516892Sodium BicarbonateHCID 219423135-Amino-2-(4-hydroxypiperidin-1-yl)benzonitrileHCID 22228218Tert-butyl(chloro)diethylsilane

Produkt 1

HCID 222282225-Amino-2-(4-tert-butyldimethylsilyloxypiperidino)benzonitrileAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Amino-2-(4-hydroxypiperidino)benzonitrile (4.0 g), tert-butyldiethylsilyl chloride (3.0 g) and imidazole (1.6 g) were stirred in dimethylformamide (20 ml) at room temperature for 1 h. The reaction mixture was treated with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The residue was recrystallized from n-hexane to give the title compound (4.2 g), melting point: 88–90° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-7298e0a646fe43e2b78b7ca4a631d47f
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

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